Acetic Acid → HCID 71526357, compound

Participants

Reaction Steps

3-(8-(6-(2-methylpyrrolidin-1-yl)pyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzaldehyde (28 mg, 0.070 mmol) and piperidine (7 mg, 0.077 mmol) were dissolved in 1,2-dichloroethane (8 mL), stirred for 1 h, then sodium triacetoxyborohydride (44 mg, 0.21 mmol) was added followed by AcOH (0.1 mL). After 15 h, the solvent was removed and the residue was purified by chromatography (silica gel, dichloromethane/methanol 40/1) to give N-(6-(2-methylpyrrolidin-1-yl)pyridin-2-yl)-6-(3-(piperidin-1-ylmethyl)phenyl)imidazo[1,2-b]pyridazin-8-amine (17 mg, 21%) as an orange solid. 1H NMR (300 MHz, CD3OD): δ 8.80 (s, 1H), 8.00 (s, 1H), 7.91-7.84 (m, 2H), 7.59 (s, 1H), 7.48-7.41 (m, 3H), 6.30 (d, 1H, J=7.8 Hz), 6.09 (d, 1H, J=8.4 Hz), 4.30-4.26 (m, 1H), 3.60-3.43 (m, 4 h), 2.51-2.47 (m, 4 h), 2.15-2.05 (m, 3H), 1.78 (brs, 1H), 1.63-1.60 (m, 4 h), 1.51-1.46 (m, 2H), 1.19 (d, 3H, J=6.3 Hz). LC-MS: [M+H]+, 468, tR=1.397 min, HPLC: 99.52% at 214 nm, 98.65% at 254 nm, tR=5.76 min.

Provenance & Evidence